Oils and lubricants, once extracted after use from a mechanical system, can hardly be reused, and should be refurbished or replaced in most applications. New methods of in situ oil and lubricant efficiency monitoring systems have been introduced for a wide variety of mechanical systems, such as automobiles, aerospace aircrafts, ships, offshore wind turbines, and deep sea oil drilling rigs. These methods utilize electronic sensors to monitor the “byproduct effects” in a mechanical system that are not indicative of the actual remaining lifecycle and reliability of the oils. A reliable oil monitoring system should be able to monitor the wear rate and the corrosion rate of the tribo-pairs due to the inclusion of contaminants. The current study addresses this technological gap, and presents a novel design of a tribo-corrosion test rig for oils used in a dynamic system. A pin-on-disk tribometer test rig retrofitted with a three electrode-potentiostat corrosion monitoring system was used to analyze the corrosion and wear rate of a steel tribo-pair in industrial grade transmission oil. The effectiveness of the retrofitted test rig was analyzed by introducing various concentrations of contaminants in an oil medium that usually leads to a corrosive working environment. The results indicate that the retrofitted test rig can effectively monitor the in situ tribological performance of the oil in a controlled dynamic corrosive environment. It is a useful method to understand the wear–corrosion synergies for further experimental work, and to develop accurate predictive lifecycle assessment and prognostic models. The application of this system is expected to have economic benefits and help reduce the ecological oil waste footprint.